Vacation rentals in Middletown

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Top-rated vacation rentals in Middletown

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Top guest favourite
A spacious living area is highlighted by rustic decor, featuring a large leather sectional sofa and a dark wooden coffee table. A recliner is positioned nearby. Three framed prints adorn the wall. A kitchen area with wooden cabinetry is visible in the background.
Home in Middletown
4.99 out of 5 average rating, 136 reviews

Western Mine Retreat near wine country

This private vacation retreat is located just 20 minutes from Calistoga in Middletown, CA. Decorated in a rustic mining-theme after the historic area, this large living space is enhanced by a 60'x15' covered deck with relaxing views of the woods and a pond just down the hill. Amenities include high speed WiFi, a large smart television, and game tables. Nearby attractions include wine tasting, hot springs resorts, quaint downtown Middletown, and the Twin Pines Casino (just down the street).

Top guest favourite
A warm living space features wooden paneling and natural light from large windows. A comfortable chair sits beside a small wooden table, and a piano is positioned nearby. Decorative plants hang from the ceiling, complemented by a cozy fireplace and a bookshelf in the background.
Home in Forestville
4.96 out of 5 average rating, 298 reviews

Forest Cozy Home

My house in Forestville is a walk to the river (Steelhead County Beach), near endless wineries, canoe rentals, gorgeous Sonoma coast beaches, Santa Rosa airport, a bicycle trail through West County with bike rentals in downtown Forestville offering immediate access to the trail, and a very well-stocked little grocery store a 5-minute walk down the hill. Lovely back roads take you to Healdsburg to the north or Sebastopol to the south. My dog & I stay in a basement studio when guests are here.

Guest favourite
A rustic cabin is nestled among tall pine trees, featuring a red exterior and a welcoming American flag mounted on the front. Sturdy stairs lead up to a spacious deck surrounded by lush greenery, providing an inviting retreat.
Cabin in Middletown
4.85 out of 5 average rating, 123 reviews

Cozy PET-FRIENDLY 1 bd cabin w/ indoor fireplace

Welcome to Castlewood Cabin in the beautiful Whispering Pines community on Cobb Mountain. Wrapped in a forest of pine trees, this rustic, refinished cabin offers one bedroom and one bathroom as well as a fold out sofa in the living room. With room for up to 5 guests this cabin is the ideal spot for a romantic couples getaway, a family road trip or even a small group of friends. Come enjoy all that Lake County has to offer - hiking, biking, boating, fishing, wineries, casinos Harbin and more!

Top guest favourite
The studio cottage features a balanced layout with a queen bed highlighted by wooden furnishings. A small desk and an ergonomic chair are positioned near a wall-mounted television. Natural light illuminates the space through two windows, creating a comfortable environment.
Guesthouse in Santa Rosa
4.89 out of 5 average rating, 1,200 reviews

Clean Comfy Cottage Downtown

Our tree shaded studio cottage is one block from the heart of downtown. Stay just a two block walk from Russian River Brewing. This clean and quiet cottage has a full kitchen, a comfortable queen bed. I am happy to customize the space to your needs. I offer soft and firm mattresses. I use cotton blankets so that you can have any weight on your bed that you would like. You are welcome to stack seven or more blankets at a time. I will adjust my cleaning regimen to meet your preferences.

Guest favourite
A clear blue sky is depicted above a serene lake, with two mountains rising in the background. Sunlight reflects off the water's surface. Leafy branches from nearby trees frame the scene, adding hints of green against the vibrant blue.
Home in Clearlake Oaks
4.93 out of 5 average rating, 138 reviews

Oak Hill Cottage: WiFi, Views

This peaceful cottage sits on an oak dotted hill overlooking the lake and offers sweeping panoramic views from almost every room in the house. It would make a great homebase for adventures fishing, boating, hiking, winetasting, etc. Travel less than one minute by car (5 on foot), & you'll find a park, a public beach, & a free boat launch. Or, you can stay home & cook a meal in its deluxe kitchen. King size beds in both bedrooms. Restaurants, coffee, & shopping within easy walking distance.

Top guest favourite
The living area features exposed wooden beams and a cozy stone fireplace at its center. Natural light fills the space through multiple windows, with comfortable seating arranged around the hearth. A warm plaid blanket is draped over a wooden couch, enhancing the cabin's rustic charm.
Cabin in Cobb
4.94 out of 5 average rating, 112 reviews

Cozy vintage cabin with fireplace near hot spring

Our rustic wood cabin is nestled among pine trees in the little village of Cobb Mountain, close to Harbin hot springs, Clear Lake, and just north of Napa valley wine country. Enjoy being surrounded by forest while you relax in the hammock or bbq on the deck. Step back in time in the vaulted wood rooms, warm fireplace, modern amenities including A/C and comfy bedding. A short walk to the swimming pool, little stream, general store and cafe. A perfect romantic getaway, or for the whole family!

Top guest favourite
A vase filled with bright sunflowers, orange lilies, and roses stands at the center of a wooden table. Behind it, a framed watercolor painting featuring sunflowers is displayed on a light gray wall, complementing the green wall to the left. A lamp casts a warm glow in the corner.
Home in Middletown
4.93 out of 5 average rating, 147 reviews

Emerald Lodge

I just updated what was the "Locust Lodge" to the "Emerald Lodge"! Now let's see if this name sticks or I change it to "Lime and Tequila Lodge", and.. still.. open to suggestions. I decided to paint one of the walls green, and upgraded a few other things that I am sure you will appreciate. There is a new memory foam mattress, flat screen TV, desk, table with four chairs, all sorts of new kitchen accoutraments, a gorgeous water color painting from a friend of mine, and lots of love.

Top guest favourite
A bright interior space features large windows offering views of the lake and mountains. A wooden desk is positioned next to a chair, with a telescope nearby, inviting relaxation and exploration. Natural light fills the room, complemented by neutral-colored furnishings and soft carpet.
Home in Clearlake Oaks
4.97 out of 5 average rating, 338 reviews

Top of the World View of Clear Lake and Mountains

If you’re looking to getaway, this home high in the hills surrounding beautiful Clear lake, is the retreat for you! Enjoy panoramic views of the lake and mountains. Very quiet, the perfect stop between the redwood trees and the Bay Area Relax on the deck shaded by mature oak trees and watch the osprey’s gliding below you or use the house as a jumping off point. Mendocino National Forest, just 20 minutes away, offers endless possibilities: mountain bike and explore the local trails

Top guest favourite
The exterior of a rustic winery building is featured, characterized by its earthy tones and distinctive red door accents. Lush greenery and blooming purple flowers surround the structure, enhancing its natural setting. The building's design includes terracotta roofing and large windows that invite an abundance of natural light.
Farm stay in Healdsburg
4.97 out of 5 average rating, 651 reviews

Gracianna Winery Vineyard Loft - Farm Stay

Costs vary based on availability. Luxury estate loft in Gracianna Winery's vineyard on Westside Road's Miracle Mile of Pinot Noir in Healdsburg includes equipped kitchen with new gas Wolf Range. Pick up breakfast needs before arriving. Vineyard machines may work overnight with lights & disruptive noises, especially during the summer and harvest is in late August early Sept. TASTING ROOM CLOSED DECEMBER 1 - MARCH 31. LOFT AVAILABLE YEAR ROUND. TOT #3294N

Guest favourite
A charming countryside house is situated under the shade of large oak trees. The exterior features a neutral-coloured façade with multiple windows. A redwood deck leads to the front door, providing a welcoming entryway. The surrounding landscape showcases dry grass and open space.
Guesthouse in Middletown
4.87 out of 5 average rating, 178 reviews

Countryside Cottage

Escape to our charming countryside oasis near the beautiful Mayacama mountain range. This small, comfortable house offers the perfect getaway just a short drive from the renowned Harbin Hot Springs. Located only 2 minutes from Twin Pine Casino. Whether you're planning a romantic couples getaway, a memorable family vacation, or a fun-filled trip with friends, our cozy haven provides the ideal setting. Book your escape now and experience the countryside.

Top guest favourite
A hot tub is positioned on a grassy area, offering a view of rows of grapevines against a serene sunset. Colorful flowers are visible nearby, complementing the natural surroundings.
Home in Healdsburg
5 out of 5 average rating, 217 reviews

10-Acre Vineyard Cottage w/Hot Tub + Bocce Court

Escape to a private and peaceful retreat surrounded by Russian River Valley Chardonnay and olive trees. Set on 10 acres of producing vines, our cottage offers vineyard views, a bocce court, fire pit, garden, cruiser bikes, and a sparkling hot tub. Immerse yourself in world-class food, wine, cycling, and nature. Guests staying 3+ nights will receive a complimentary bottle of Chardonnay crafted from our vines. Your perfect wine country escape awaits!

Guest favourite
A modern kitchen and dining area feature a large wooden table surrounded by black chairs. The kitchen is equipped with stainless steel appliances and sleek cabinetry. Natural light floods the space through large windows, highlighting the wood-beamed ceiling and minimalist decor.
Cabin in Cobb
4.96 out of 5 average rating, 105 reviews

Wrenwood Cabin | Modern Mtn Home

Welcome to our newly renovated modern farmhouse cabin, nestled on a private acre surrounded by majestic 200-foot Douglas Firs. Enjoy the seasonal creek that graces the backyard during the wet season, providing a tranquil retreat. Perfect for a peaceful escape or productive remote work, our cabin features high-speed internet and modern amenities. Explore Cobb Mountain’s hiking, biking, and swimming adventures, all just a short distance away.

Popular amenities for Middletown vacation rentals

Quick stats about vacation rentals in Middletown

  • Total vacation rentals

    Explore 10 vacation rentals in Middletown

  • Nightly prices starting at

    Middletown vacation rentals start at $137 CAD per night before taxes and fees

  • Verified guest reviews

    Over 1,500 verified reviews to help you choose

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    10 of Middletown vacation rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Middletown rentals

  • 4.9 Average rating

    Middletown stays are highly rated by guests—averaging 4.9 out of 5!

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